Microbial transformation of steroids. XIX. Transformation of steroids by Mycobacterium flavum.

Abstract

In studying the transformation capacity of the strainMycobacterium flavum no. 390 it was shown that steroids of the androstene series (Δ4-androstene-3,17-dione and testosterone) are transformed to their corresponding 1-dehydro derivatives. Dehydrogenation at position 1-2 was simultaneously demonstrated by an oxidoreduction process at C17. In steroids of the pregnene series in which C17 is not occupied by a hydroxy group (progesterone, its 20β-hydroxy derivative, 11-deoxycorticosterone) the primary reaction taking place is the splitting off of the side chain at C17; giving rise to Δ4-androsten-3,17-dione. The subsequent reaction is dehydrogenation at position 1-2 which is accompanied by an oxido-reduction process at C17. In steroids of the pregnene series with a hydroxy group at 17a position (steroid “S”, cortisone, prednisone) the side chain at C17 is never split off. The primary reaction taking place there is the dehydrogenation in position 1-2. The 1-dehydro derivative thus formed is, however, further reduced in position C20 to the corresponding 20β-hydroxy -1- dehydroderivative of the original steroid. After prolonged fermentation (48 hrs.) the transformation proceeds to apparently nonsteroid compounds.